可见光诱导的失活 C(sp)-H 键的单氟烯基化和二氟烯丙基化反应通过 1,5-氢原子转移 (HAT)。
Visible-Light-Induced Monofluoroalkenylation and -Difluoroallylation of Inactivated C(sp)-H Bonds via 1,5-Hydrogen Atom Transfer (HAT).
机构信息
Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Science, Zhejiang Normal University, 688 Yingbin Road, Jinhua 321004, P. R. China.
College of Chemistry and Chemical Engineering, Henan University, Kaifeng 475004, P. R. China.
出版信息
J Org Chem. 2023 Mar 17;88(6):3883-3896. doi: 10.1021/acs.joc.3c00144. Epub 2023 Mar 7.
The direct monofluoroalkenylation of C(sp)-H bonds is of great importance and quite challenging. Current methods have been restricted to the monofluoroalkenylation of activated C(sp)-H bonds. Here, we reported the photocatalyzed C(sp)-H monofluoroalkenylation of inactivated C(sp)-H bonds with -difluoroalkenes via 1,5-hydrogen atom transfer. This process shows good functional group tolerance, such as halides (F, Cl), nitrile, sulfone, ester, and pyridine, and good γ-selectivity. Moreover, this method succeeds in the photocatalyzed -difluoroallylation of inactivated C(sp)-H with α-trifluoromethyl alkenes.
C(sp)-H 键的直接单烯氟化具有重要意义且极具挑战性。目前的方法仅限于活化的 C(sp)-H 键的单烯氟化。在这里，我们通过 1,5-氢原子转移报告了用光催化的 -二氟烯对非活化的 C(sp)-H 键的 C(sp)-H 单烯氟化。该过程显示出良好的官能团耐受性，例如卤素（F、Cl）、腈、砜、酯和吡啶，以及良好的γ选择性。此外，该方法还成功地用光催化的α-三氟甲基烯烃对非活化的 C(sp)-H 进行了 -二氟烯丙基化。
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